Regional Sales Director, Platform

We’re obsessed with making hard work pay off, for our people, our customers, and the world around us. As a Fortune 500 company and a leading AI platform for managing people, money, and agents, we’re shaping the future of work so teams can reach their potential and focus on what matters most.

About the Team Workday is building a new specialized sales team focused on selling platform, data, analytics, AI, and extensibility solutions into the Office of the CIO. This team will partner with enterprise customers to help IT leaders modernize their technology strategies, unlock business value from Workday’s platform, and align innovation roadmaps to strategic business outcomes.

About the Role You are an experienced enterprise sales leader who combines technical fluency, executive presence, and disciplined sales execution. You have led teams through complex, multi-stakeholder sales cycles and are comfortable engaging directly with CIOs, CTOs, and senior IT leaders.

Key Focus & Responsibilities

• Team Leadership & Coaching: Use your experience to lead, coach, and mentor a field sales team of specialized Account Executives. Drive a culture of accountability, performance, and continuous development.
• Deal Strategy & Orchestration: Lead a team focused on driving complex platform sales cycles ($500K+ ARR) by orchestrating internal teams of pre-sales, value management, bid management, and sales support from initial discovery through negotiation and closing.
• SOW, Roadmap, & Deal Governance: Oversee your team's operational accountability for generating and executing formal AI/Platform Statements of Work (SOWs) and delivering 1–3 year phased technology roadmaps.
• Forecasting & Business Modeling: Maintain accurate forecasting data and business modeling for senior leadership, while helping your team operationalize a "time to engage" strategy based on corporate triggers.
• Hyperscaler & Partner Co-Selling: Employ effective selling strategies by pulling together different business units to maximize sales, guiding your team to co-sell joint platform solutions with cloud hyperscaler partners (AWS, GCP) and Global System Integrators (GSIs).

Basic Qualifications

• 8+ years experience selling cloud/SaaS/ERP/analytics solutions, with a specific focus on complex platform, enterprise data, or AI/analytics solutions directly to the Office of the CIO or CTO.
• 8+ years experience managing complex sales cycles from start to finish with a track record of successful revenue/quota attainment.
• 5+ years experience as a leader in a team selling environment.

Other Qualifications

• Domain & Technical Fluency: Strong technical credibility in modern enterprise IT architectures, cloud data foundations, API orchestration, data privacy/security, and AI/ML platform integration.
• oCIO Persona Fluency: Speaks the language of IT leadership. Understands the strategic competitive landscape by staying up to date with trends and customer needs so you can effectively coach your team to position Workday solutions.
• Cross-Functional Orchestration: Proven experience pulling together different business units to maximize on sales and position Workday's extensibility, analytics, and autonomous agent capabilities as an interoperable component of a client's wider IT stack.
• Dynamic Leadership: Self-starter attitude with the ability to work in a dynamic environment, empowering your team to challenge legacy IT assumptions, frame clear TCO models, and align technology roadmaps to strategic business goals.

Workday Pay Transparency Statement Workday pay ranges vary based on work location. As a part of the total compensation package, this role may be eligible for the Workday Bonus Plan or a role-specific commission/bonus, as well as annual refresh stock grants.

Primary Location: CAN.ON.Toronto Primary Location Base Pay Range: $170,000 CAD - $255,000 CAD